


A Challenge

by AnaliseGrey



Series: Moonbeam, Blossom, and Spark [3]
Category: Critical Role (Web Series)
Genre: Anal Sex, Blow Jobs, Choose Your Own Ending, MORE SMUT!, Magic Bondage, Multi, Orgasm Delay/Denial, Rope Bondage, The amount of gold dust Essek goes through regularly must be incredible, better living (and sex) through magic, sexy challenges
Language: English
Status: Completed
Published: 2020-11-21
Updated: 2020-11-21
Packaged: 2021-03-10 05:22:35
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 8,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27658120
Author URL: https://archiveofourown.org/users/AnaliseGrey/pseuds/AnaliseGrey
Summary: He doesn’t know how he gets himself into these kinds of situations.Well.That’s not entirely true.Despite what he’d once told the Nein, he does in-fact have a favorite color, and it seems that the people he knows who happen tobethat color make it their business to cause him problems.Delightfulproblems, but problems nonetheless.
Relationships: Mollymauk Tealeaf/Essek Thelyss/Caleb Widogast
Series: Moonbeam, Blossom, and Spark [3]
Series URL: https://archiveofourown.org/series/2013718
Comments: 8
Kudos: 71





	1. Chapter 1

**Author's Note:**

> This fic is brought to you by the letter 'I' for 'Indecision'!
> 
> I had the main idea for this fic, but couldn't decide what I wanted the outcome to be. So, I wrote both!
> 
> At the end of this chapter, you get to choose which path to take.

He doesn’t know how he gets himself into these kinds of situations.

Well.

That’s not entirely true.

Despite what he’d once told the Nein, he does in-fact have a favorite color, and it seems that the people he knows who happen to _be_ that color make it their business to cause him problems.

_Delightful_ problems, but problems nonetheless.

He knows he’s in trouble when he’s pulled out of his reading fugue by hushed words- Molly and Essek across the sitting room, whispering to each other. Molly’s perched on a large cushion at Essek’s feet, his arms folded and resting on Essek’s knees as he leans in. It’s possible they’re merely staying hushed so as not to bother him, but they keep glancing over before whispering again, Molly’s tail flicking back and forth in a manner Caleb is well-familiar with.

Like he said- problems.

He pretends not to notice, knowing that when they’re ready, they’ll make whatever plan or scheme they have known, and it won’t do him any good to try to pry it out of them before they’re ready.

He manages to sink back into his reading, so it catches him by surprise to suddenly feel fingers threading through his hair. Blinking owlishly, he looks up and the fingers in his hair tighten, tugging his head gently back. When he looks up it’s to find Essek smiling at him, upside down from Caleb’s point of view.

“How are you enjoying your book?”

“It’s proving quite enlightening. Learning quite a lot about Tallman’s Line and the-”

Essek’s hand covers his mouth, muffling his last few words. Caleb quiets, and once he does Essek slides his hand down to pet over the line of Caleb’s throat, his other hand still tangled in Caleb’s hair. It takes Caleb a moment, but then- 

_Oh_.

Essek doesn’t actually want to know about the book.

“It’s good.”

Essek’s smile grows incrementally, impossibly fond, and Caleb catches a glint of fang before he’s distracted by two hands landing on his knees, then slide higher. He can’t move his head yet, but when he turns his eyes down it’s to find Molly, grinning up at him from where he’s kneeling between Caleb’s feet.

He swallows, then looks back up at Essek. “I feel as if I’m being ganged up on.”

“Hmm. But only in the best possible way.” Leaning down, Essek lets go of Caleb’s hair and pulls him back with a light hand on Caleb’s throat. He places a kiss on Caleb’s forehead, then draws back again. “Would you like to play a game with us, my spark?”

He can just barely see Molly’s tail, waving back and forth behind the tiefling at the edge of his peripheral vision, and when he swallows this time, his mouth is much dryer.

“What sort of game?”

“Do you recall at one point we discussed the possibility of setting a challenge for you- of maintaining concentration under gentle, loving duress?”

Caleb blinks, thinking, and when it hits him he flushes at the sense memory- the weight of Molly’s cock in his mouth, his thighs twitching and straining under Caleb’s hands, the delicious stretch of Essek slowly pushing in to his ass-

“ _Ja_ -” Caleb coughs, clearing his throat. “ _Ja_ I remember that.”

“I thought you might.” Essek cards his fingers through Caleb’s hair again. “Are you game?”

Caleb’s stomach gives a pleasant flip, and he's nodding before he can verbally answer. “Yes, sir.”

“Excellent. We’ve had some thoughts.”

Molly grabs Caleb’s hands to help lever them both up, and Caleb’s mind catches on the ‘we’.

_Scheiße_.

He lets himself be pulled along to the bedroom, book forgotten, and the other two quickly divest him of his clothes. He notices neither of them get undressed, and when he quirks a brow in question he only gets two enigmatic smiles in return.

“Not necessary for this part,” says Essek.

“Though perhaps later,” adds Molly.

They move to the bed, having Caleb lay on his stomach head pillowed on his arms as if for a massage, with the other two sitting on either side of him. Essek pets a warm hand down Caleb’s spine and Caleb melts under the attention, giving a pleased hum.

“I suppose the first question I should ask is whether you have Alter Self in your repertoire, today.”

After a quick mental check, Caleb nods. “I do.”

He feels Molly wiggle in excitement next to him, his glee catching, and Caleb finds himself smiling even though he doesn’t quite know what’s going on.

“Then, my spark, what I would like you to do,” Essek says, hand rubbing at the base of Caleb’s spine. “Is give yourself a tail, like our blossom has. I’m sure you can recall how it felt when you two were tethered and I played with his. Imagine how it will feel when it’s yours.”

Caleb shudders, overcome again by memory. He couldn’t see what Essek was doing, but he _does_ in fact recall what it had felt like. Confusing, first and foremost, since he didn’t _have_ a tail at the time, but could still distinctly feel Essek touching Molly’s. The feel of it- he doesn’t know how to describe it. It wasn’t the same as someone touching his cock, which is understandable; if all tieflings’ tails felt that way, he imagines nobody would ever get anything done. It was incredibly sensitive, like the pulse point of his wrist, or his inner thighs just before they meet with his hip; not normally an erogenous zone, but in the proper circumstances-

He gives a shiver, and nods in understanding. “And what of this ‘gentle, loving duress’?”

“Well, you see that’s where I come in.” Molly flops onto his belly next to Caleb, feet up and kicking in the air as his tail loops in delighted curlicues behind him. “You’ve spent a great deal of time since I’ve known you torturing me with my own tail, and I feel it’s only fair that I get to return the favor.”

“And so here’s the game.” Essek resumes petting Caleb, stroking from neck to waist. “You are going to give yourself a tail, like our Molly’s. That is when the clock starts. If you can keep the tail the whole duration of the spell, then you get to come.”

“And if I don’t?”

“If you lose concentration, and therefore the tail, before the natural end of the spell, then I put you in a cock cage until I see fit to let you out again, and tie you up for blossom and I to have our wicked way with you.”

Molly lets the spade tip of his tail drag up the back of one of Caleb’s thighs, making him squirm. “I get to come either way, so this is win-win for me. Whether you _also_ win is up to you.”

Caleb licks his lips, feeling his pulse already starting to quicken.

“Oh, and one more thing-” Essek leans down so he can whisper in Caleb’s ear. “If you come before the hour is up, the same penalty applies.”

“Fair,” Caleb says, voice gone breathy.

Essek moves up to the head of the bed, getting comfortable amidst a pile of pillows, and has Caleb scoot up a bit further and angle himself so his head is near him. Off to the side, Molly waits, and the movement of his tail puts Caleb in mind of Frumpkin about to pounce on an unsuspecting mouse, and realizes the comparison is very apt.

Running his fingers through Caleb’s hair again, Essek smiles, showing more than just a hint of fang this time.

“At your leisure, then, my spark.”

With a muttered word and a twist of his hand, Caleb casts, and the clock starts.

**Notes for the Chapter:**

> If you want to see Caleb succeed, go to [chapter 2](https://archiveofourown.org/works/27658120/chapters/67678961)!
> 
> If you want to see Caleb fail, go to [chapter 3](https://archiveofourown.org/works/27658120/chapters/67678997)!


	2. Chapter 2

He makes his tail purple, modeling it after Molly’s.

It’s the tail he’s most familiar with, because Molly’s right, he _has_ spent a lot of time paying very close attention to it. He makes sure to capture the ridges up near the base, the gentle taper down towards the bottom, and the delicate spade coming to a point at the end. It lacks the piercings that Molly’s has, but he thinks it will do.

Movement takes a moment to master, but soon he has the hang of it, waving and flicking it like he’s seen Molly do.

And as Molly has apparently seen _him_ do, he catches it mid-wave, holding it gently in one hand.

“Wow-” Molly’s examining it, and Caleb flexes, letting it undulate in Molly’s hands. “Oh...this is going to be fun. Time to test how true to life this thing is.” Without letting go, Molly lets his right hand slide upward, and Caleb shivers at the sensation.

“How does it feel, my spark?”

“New? It’s taking some getting used to, but _nng-._ ” Caleb stops mid-sentence, hands fisting in the bedding. Molly’s made his way to the ridges, and is experimentally poking and rubbing at them.

“Tell me, Caleb, does this feel the same as it did when moonbeam over there was doing it to me?” He takes one of the ridges closer to Caleb’s spine and drags his thumb over it, pressing and massaging, and Caleb lets out a gasping whine.

“ _Yes_ \- yes it does. Just- more immediate.”

“Huh. Neat.” Molly does it again, and Caleb’s eyes scrunch shut, trying to get control of himself.

“Oh, but you are sensitive, aren’t you?” Essek leans down so he’s more eye-level with Caleb. “Is our blossom making you feel good, pet?”

It takes a second for Caleb to answer, waiting to do so until he thinks he can speak without it coming out as moan.

“He is, yes.”

“Well I am the resident expert, aren’t I, dear?”

Molly continues to toy with him, paying special attention to the spade, and Caleb thinks he’s going to have to remember this. If he’d realized how much sensation it had, he’d have used it against Molly ages ago.

He catalogs everything Molly does, trying to use it to distract himself, knowing that whatever Molly is doing, he’s likely doing because he knows how devastatingly-effective it is. And so he memorizes- the light nibbles at the spade, Molly’s forked tongue wreaking havoc on Caleb’s nerves as he teases. The lightest possible scrape of fangs pulls a moan from him, and Caleb has to remind himself to breathe. Molly continues upward, gently massaging, and while it’s not as intense as the end or the base, it still feels incredible.

As Molly gets closer to the base of Caleb’s tail, he looks up at Essek. “Sir, I have a couple of requests and suggestions. If I may.”

Caleb appreciates the short break, using it to gather the bit of shredding self-control he has, though he’s not encouraged by the interested expression on Essek’s face.

“And what are your requests and suggestions, my lovely plum blossom?”

“First, I was wondering if we could have Caleb tell us occasionally how long is left. I want to be sure I give this my best effort, you understand, and knowing how much time I have would be helpful.”

Essek’s expression slides from interested to amused, and he nods, waving a hand magnanimously. “Granted. And the second?”

Caleb can’t see Molly’s face, but he can hear the wicked smile in his voice when he asks, “I don’t suppose you have a way to keep him from thrashing around, do you? This is about to get very intense.”

He can’t imagine what Molly is going to do that he would classify as _more_ intense than what he’s already been doing, but he’s about to find out.

“I believe that can be arranged, blossom.” Turning to Caleb, Essek raises an elegant eyebrow. “Spark, if you would, please stretch your arms out ahead of you, wrists together.”

He can’t help the whine as he does it, but he complies, arranging his arms as requested.

Essek mutters something under his breath and moves his hands together as of scooping then patting something down, and Caleb feels the press of Essek’s magic on him, the gravity around his wrists suddenly strengthening tenfold with pinpoint accuracy. He tries to tug his hands loose, and gets absolutely nowhere. He has to drop his head between his arms for a moment at that, the sudden vulnerability only making his arousal spike unhelpfully.

He’s distracted from that line of thought by Molly throwing a leg over both of his so he’s straddling the back of Caleb’s thighs. He sits, effectively pinning Caleb’s lower body.

“You’ve put all these lovely little ridges on, Mr. Caleb.” Molly lightly runs his fingertips over the top of them, letting them skip from bump to bump. “I feel it only fair to take the time to appreciate each and every one of them.” 

Caleb tries to buck under him as Molly’s fingers trail along, but can’t with Molly sitting on him. The most he manages is a slight wiggle, which does him no favors, rubbing his cock against the bedding beneath him.

“Before I begin, though, how much longer do I have, dearest?”

“Approximately...half an hour.” He’s panting, the combination of Essek’s magic, Molly pressed so close, and what Molly’s been doing to him making it difficult to concentrate.

Difficult, but not impossible; and he’s concentrated through far worse things than this.

He takes a deep breath, letting it out on a shudder as Molly begins his offensive.

Molly is good as his word, spending minutes at a time on each of the ridges, and by the time he hits the third, Caleb can’t keep the sounds he’s making contained. This is cruel- cruel and unusual, and he’s already planning what he’s going to do to Molly in recompense. _He’s_ going to lose his tail at some point within the hour, but Molly won’t be losing _his_ , and Caleb is going to make him regret showing all his weak spots.

As it is, in the meantime, he’s struggling to hold on, giving time reports when asked, and doing anything he can think of to maintain control, both of his spell, and his hips, which keep wanting to buck and grind into the mattress below. He knows if he starts moving now, he might not be able to stop, and he isn’t looking forward to finding out how long Essek would keep him locked up and wanting. Best thing is to just not move at all, really.

Halfway through his exploration, Molly slides off Caleb’s legs, and without even being asked, Essek casts again, a similar gravity field dropping over the back of Caleb’s thighs, pinning him in place.

“Thank you, sir! Very helpful,” Molly says, and then leans over from where he’s sitting on his knees, and carries on.

Caleb’s close- in more ways than one- and he knows his margin for success is incredibly thin, and getting thinner the more Molly teases; he’s using his mouth now, sucking on the ridges like he would a nipple, and the resulting sensation is very similar. It zings up Caleb’s spine, making him gasp and squirm to the extent he can, and he’s glad of the magic pinning him, keeping him from moving more than he means to.

He shouts as Molly sucks another of the bumps while gently trailing his claws up and down over sensitive skin, and he can feel the seconds slipping by. It’s under a minute, and he tells them so, not wanting them to think he’s lost concentration. Molly makes the most of it, catching the end of the tail and beginning to tease the spade with his fingers, rubbing at the especially sensitive place where the tail meets the base of it, while continuing to suck and nibble on the top-most ridge.

It’s so much- it’s _too_ much, really- but somehow Caleb not only hangs on, but manages to count down the last ten seconds before the tail vanishes under Molly’s hands. All Caleb can do is lay there for a moment, still incandescent with need, but unable to do anything to relieve it.

“Well damn.” Molly moves up to sit next to Essek so Caleb can easily see them both, and he’s pouting. “I almost had him.”

“I know, pet. But don’t worry. I’m sure this won’t be the last time we play this sort of game.” He looks over at Caleb, face flushed and still trying to move against the hold of Essek’s gravity fields now that the hour has passed and he doesn’t have to worry any longer. “My spark, was there something you wanted? You did so well for us, I feel it only fair that you get to share in the reward with our blossom.”

It’s difficult to think clearly, arousal still coursing through him, but he manages to gasp out, “Molly- I want- if he- please, sir.”

Questioningly, Essek looks at Molly, and Molly grins. “A genuine pleasure.” He looks down, trying to catch Caleb’s eye. “What are you in the mood for?”

“ _Anything_.” Caleb keeps eye contact, eyes blazing with want. “Anything, just- I want you, Molly, please.”

“Well how can a person say no to that?” Molly wiggles over until he can easily hop off the bed, and turns to Essek. “Permission to proceed, sir?”

Essek’s lips tip up in a smile, and he nods. “Permission granted, little blossom.”

Molly lets out a happy noise, and strips with a quickness that speaks of practice. He wanders, happily naked, to their supply cabinet, tail once more moving in pleased swoops behind him. He retrieves a vile of his favorite oil, and comes back to the bed, looking to Essek.

“What are my options, sir? Take care of it myself, have you do it, or-?”

“Hmm.” A considering look crosses Essek’s face, and he digs in the pocket that his components reside in. “I don’t believe you’ve had the pleasure of this experience yet, and I know how you relish new things. Up on the bed, drop the vial next to you. All fours, please.”

While Molly climbs up, Essek relaxes the gravity just enough to let Caleb flip over, and then brings it down again, pinning his wrists up over his head, and keeping his thighs pressed down where they are, though slightly spread.

Once Molly’s on the bed, Essek says a few words and moves his hands, and the spell completes. Caleb gets to watch Molly’s face as he experiences something the two wizards already have; Essek’s unseen servant picks up the vial, and it disappears around behind Molly. It’s easy to tell when the servant starts working Molly open, because as per usual, Molly isn’t quiet.

“Oh _fuck me_. This is- you’ve both been holding out on me.”

He gasps and moans through the process, at one point dropping down to his elbows, though his ass remains in the air, tail lifted and curving up and over, the spade dangling near Caleb’s face.

Caleb doesn’t have the movement to reach and catch it, but he can strain up enough to stick his tongue out and catch just the edge of the spade with it.

Molly cries out, his tail rippling over them, and pulls it out of Caleb’s reach.

Soon Molly is telling Essek he’s ready, and the unseen servant relents. Molly crawls up the bed and straddles Caleb again, smiling down at him as he runs his hands down Caleb’s chest. Caleb can’t help the sound he makes as Molly’s claws gently catch and drag over his skin, and he finds he can’t stay still either, though he doesn’t get far.

“Shhh, I’ve got you.” Molly places his hands flat as he drags them the rest of the way down, then rises up on his knees to position himself properly. 

“Sir, a little help, please?”

Essek murmurs something, and Caleb catches movement out of the corner of his eye as a mage hand floats into view, dipping down between Molly’s legs. It pulls a gasp from Caleb’s lips as it takes hold of his cock, tilting it up and holding it in place for Molly to come down on. Molly gets himself into position, and with the mage hand’s assistance, he sinks down until he’s sitting mostly on Caleb’s lap, his knees snug in against Caleb’s hips. He just stays there a moment, and Caleb is about to start begging him to move when Molly does, placing one hand on Caleb’s stomach for balance as he raises himself up and drops back down.

It’s the sweetest form of torture Caleb knows, being welcomed into the delicious heat of Molly’s body but being utterly unable to move. He desperately wants to thrust up, to buck and get more, but he can’t. Somehow Molly is maintaining a slow and steady pace, and it’s driving Caleb slowly mad.

Molly swivels his hips and Caleb groans, eyes scrunching shut, then startles as a hand caresses over his neck.

“Peace, spark, it’s just me.” Essek has moved closer, drawing himself near enough that he can lean over and kiss. He keeps one hand on Caleb’s shoulder, letting the other rest over Caleb’s collarbone, and drinks down the noises Caleb makes.

Caleb’s skin feels on fire, every nerve at attention, and he starts to wonder, if this is what winning gets him, what would losing have cost him? The torment continues until he’s begging every time Essek draws back for breath, pleading for more, to be allowed to come, even as Molly is speeding up, a fine sheen of sweat making his skin glow even as his thighs tremble from exertion.

“I’m not going to last much longer, moonbeam,” Molly gasps out, panting, and Essek nods. A moment later it’s apparent that the unseen servant has joined them again, Molly giving a shout and almost folding forward onto Caleb as it wraps around his cock and gives a firm tug. The sounds Molly makes as the unseen servant jacks him off are obscene, but Caleb finds himself echoing them as Molly tightens around him with each tug.

“Fuck- Caleb, you feel so _good-_ ” Caleb knows Molly is probably close- he always gets chattier right before he comes, and this time is no different. It’s odd to see Molly coming with nothing to obscure the view, his cock pulsing and twitching as he groans, splattering Caleb’s front with spend. Caleb, for his part, is so _close_ , but can’t quite get there, and he worries, knowing he wouldn’t blame Molly if he wanted to tap out at this point.

“I‘m still good,” Molly pants, planting his hands on Caleb as the unseen servant releases him. He rocks his hips, and Caleb moans, struggling against the hold of Essek’s magic.

“Lovely spark-” Essek’s hand pets over Caleb’s chest, skimming lower to drag over a nipple. “What do you need? You’ve been so patient. How can we help you?”

“I- I don’t- **_Scheiße_ ** _._ ” He jerks as Molly tightens his internal muscles as he pushes up again, and lets out a frustrated sob.

“Perhaps a bit more stimulation is in order.” Essek purrs, and touches Caleb’s chest with intent, plucking and pinching as he knows Caleb likes.

Caleb’s about to start begging again when he chokes on his words at the light touch of something to his hole. The blasted unseen servant is back, gently teasing its way in, and Caleb shouts as it finds the bundle of nerves it was instructed to search for, mercilessly pressing against it and dragging light touches across it in turns.

Caleb’s losing his mind and coherency, and he desperately hopes the other two men can read his need in the way he trembles, in the gasps and muddled sounds that tumble from his mouth.

He’s almost there, just a bit more-

Essek gestures, and taps on Caleb’s nipple, sending a small but sharp shock through it, and that’s enough, sending Caleb hurtling over the edge. He thrashes, and he knows he’s going to be aching later, but he can’t hope to stay still as the waves of pleasure crest then crash over him, drowning him in relief.

He whines as the unseen servant gives one last swipe then withdraws, and Molly comes to gasping stillness a second later, still seated on Caleb’s cock, hands petting at Caleb’s stomach in firm sweeps.

“I’m just- I’m gonna-” Molly gets himself up on his knees again though his legs tremble, and lets Caleb slip out of him before tumbling down to the bed once he’s clear. “Fucking hell. We should do things for science more often, sir.”

Essek snorts delicately, then releases the hold the increased gravity has on Caleb.

“I think we may need to wait a little while before doing this sort of experiment again, blossom, for our spark’s sake, if nothing else.” He ducks down again, pressing a kiss to the corner of Caleb’s mouth. “How did you enjoy yourself?”

Caleb is with it just enough to smile in response, humming contentedly as he curls on his side for a short rest.

“You know me, I like a challenge.”

Essek’s gaze sharpens, and Caleb has a moment of pleasant foreboding.

“Well. We will have to see what we can do to make it more difficult, spark. Wouldn’t want you getting bored.”

There’s a chuckle behind him as Molly spoons up, draping his arm and tail over Caleb to cuddle; there’s the fizz of prestidigitation along his front- Essek dealing with the mess- and for the next little while, that’s all Caleb knows.


	3. Chapter 3

He considers making the tail purple like Molly’s, though the idea of having a purple tail when the rest of him _isn’t_ purple seems odd. Having a him-colored tail feels like it would be even weirder, though, and in the end he goes with what he knows and replicates Molly’s. Gods know he’s spent enough time interacting with Molly’s tail at this point that he has it fairly memorized, from the delicate spade at one end, the tail proper, leading up the the thickest part where it attaches to his body, the top foot and a half or so adorned with spaced ridges.

Caleb gives it a flick, delighted when it moves like he’s seen Molly’s move, but he doesn’t get to enjoy it long before Molly’s catching it in gentle hands, pulling it close to examine it. Caleb lets it ripple in Molly’s grasp, and Molly’s intrigued smile breaks into a grin.

“Well isn’t this a thing.” He trails a finger along the length of it, feather-light, and Caleb shivers, goosebumps raising up his arms in response. “You know, I think I’m going to enjoy this.”

With that, Molly sets to, Essek helping by using a mage hand to retrieve a bottle of massage oil at Molly’s request. Once he has it, he unstoppers it, drizzling a fair amount into his hands, giving the bottle over to Essek for safekeeping.

Caleb groans at the first gentle tug at the base, and it’s difficult to describe how it feels. He doesn’t have the context or experience to explain it, but that doesn’t really matter. The point is that it feels good- _really_ good- and all Molly’s done so far is grip near where it attaches and slide his hands down.

“Hm,” Molly says, then grips it a short ways down and lifts. “I wonder if you’re as sensitive-”

Caleb gives a shout and jolts as Molly swipes an oiled finger along the underside of where it meets Caleb’s body. It’s tender and sensitive in a way Caleb hadn’t expected, like the spot behind his balls, and that sort of connection makes his brain fizzle as Molly presses his advantage, teasing with gentle fingertips, letting them slide back and forth until Caleb’s writhing and panting, hands clenched in the bedding.

“I’ll take that as a definitive yes,” Molly says, grin evident in his voice.

He doesn’t know if it’s a mercy or not, but Molly stops to move to a new spot, again dragging his fingertips over each of the tail ridges in turn, and no- it’s _not_ a mercy. Each fleeting touch sends sparks up his spine, and he groans, curling in until he’s got his knees up under him, folded forward so that his forearms still rest on the bed. He thought this position would be better, since it wouldn’t let him grind into the mattress like he wants, but he quickly discovers a fatal flaw in the plan- he can’t grind into the mattress, but he’s still just low enough that the head of his cock drags lightly over the coverlet when he moves, adding a completely separate layer of torment than what Molly’s making him suffer.

And Molly is making him move a _lot_.

After running his fingers back and forth a few times until Caleb is whimpering and trembling, Molly leans forward and flicks his tongue over one, continuing to lick and nibble at it when it pulls a cry from the man under his hands.

“ _Aaah_ -” Caleb drops his head down so it falls between his arms, eyes scrunched shut, and tries to focus, to concentrate. Everything Molly’s doing, he’s doing because he _knows_ it will feel good. This just means that when the tables are inevitably turned, Caleb will be ready.

And Molly won’t have the respite of an hour-long time limit.

He’s focusing so hard on what Molly’s mouth is doing that he’s completely lost track of one of his hands, and that’s a mistake. Molly sucks on the ridge while his fingers begin rubbing gently but unrelentingly at the very end of his tail, at the base of the spade, and the air punches out of him in a surprised shout.

It’s so much- _too_ much, it turns out- and between one breath and the next, his concentration slips, and he loses the tail.

There’s a moment of stunned silence, and then it’s filled with Molly’s cackling glee.

“I win!” With nothing left to hold onto, Molly crawls forward until he’s shoulder-to-shoulder with Caleb, tilting his head down and to the side, trying to catch Caleb’s eye. Caleb, for his part, is still panting, intensely aroused, and coming to the realization that since he failed, he’s going to have to face the penalty for failure. It won’t be the _worst_ penalty he’s ever endured, but he also knows that between these two, it will sure _feel_ that way.

“My spark,” Essek purrs, moving from where he’s lounging on his pillows to come up on Caleb’s other side, running a hand from the base of his spine up to the back of his neck, squeezing gently. “It seems you were not up to today’s challenge.”

“No, sir.”

“And so you are subject to the predetermined penalty.”

He shivers. “Yes, sir.”

“Very well, then.” Essek gives the back of his neck one more squeeze, then lets go, tapping Caleb’s hip as he moves to get up. “Come along.”

Essek won’t appreciate being kept waiting, and so Caleb doesn’t dawdle, climbing over and off the bed to stand beside it, arms loose at his sides. His blood is still thrumming through him, though for a different reason, now. He’s going to suffer and he knows it, but it’s a kind of suffering he enjoys on occasion. There's an odd sort of freedom to giving into this sort of suffering, and he’d gone into this situation knowing that it was a win-win for him as well.

It was only a matter of how.

Essek returns to him a moment later, and hands something off to Molly, who’s now perched on the side of the bed, tail flicking behind him again. Caleb catches a flash of steel and swallows, mouth dry as he recognizes the cock cage Essek prefers for these sort of occasions. He doesn’t have long to contemplate it before Essek’s fingers are light on his chin, turning his head forward again.

"With me, pet.”

Essek has him sit on Molly’s vanity chair so he’s at a better height to work with, and begins binding Caleb’s arms as promised. A pair of sturdy rope cuffs are worked around his wrists, then wound between, securing them together; Caleb knows from experience that he’s not getting loose on his own. Stepping back, Essek contemplates him a moment before grabbing another length of rope, and starts winding it around Caleb’s chest, over and around his shoulders, draping over his neck, and Caleb loses track of what precisely is happening. The ropes are pulled taught, wrapped again here, twisted there, Essek’s eyes narrowing as he works. When he’s done, Caleb has a chest harness, two horizontal bands, one towards the top of his ribs and the other in line with his collarbones. A ‘v’ comes down over his shoulders, coming to it's point as it dips under the top band. What really catches his attention, though, are the three pairs of strands that connect the top band to the bottom. There’s one pair that goes down the center of his chest over his sternum, pulled into an artful twist. The other two pairs, though-

Those are arranged to run flat over his nipples, and his suspicions are confirmed a moment later when Essek pulls one of the pairs apart and reaches between to take hold of the nipple they’d been covering. He tugs and tweaks until it stands to attention and Caleb whines as Essek arranges the strands to either side so that they squeeze lightly when he sits up straight. Essek does the same to the other, then puts a finger to his lips, again contemplative.

“Blossom, what do you think- clamps or no?”

Caleb can’t help the whimper at the mere mention of them, and that seals his fate more than anything, Molly’s expression going wicked.

“He’ll look very pretty in them, sir.”

“That he will. Please grab a set from the cabinet, your choice.”

Molly scrambles to comply, and Caleb tries to prepare himself. He loves and hates the clamps in equal measure, similarly to how he’s going to feel about the rest of this, he imagines. He’ll suffer in the short term, but longer term he'll enjoy it.

A moment later, Molly stops at Essek’s side, and Caleb opens his eyes to see what Molly’s chosen. He has a moment of relief when he sees the simple drawstring loops in Essek’s palm, but then whines in dismay a second later when Molly grins at him while dropping a couple small weights into Essek’s hand as well.

Essek raises an elegant eyebrow at Molly’s choice. “Feeling a bit mean this evening, are we, blossom?”

“It _is_ a penalty. Sir.”

“That is is.” Essek’s lips quirk up in a smile, and he hands everything but one of the small loops back to Molly to hold. Tugging on the loop to make it bigger, he takes hold of Caleb’s nipple again, tugging until he can fit the loop around it easily, and slides the bead on it up to cinch it. Caleb hisses as it does, doing his best to hold still, though it becomes more difficult when the other goes on. There are little metal hoops at the bottom of each drawstring, and it’s to these that the weights are attached. Molly isn’t feeling _too_ mean, it seems. There’s only the two, one per clamp, and they’re some of the smaller ones in Essek’s collection. Caleb breathes through it, knowing that very shortly these will be the least of his worries.

“Blossom, the cage if you please.”

Essek has Caleb stand so he can sit, Caleb moving to stand between his spread knees. Looking up at Caleb, Essek runs his palms up Caleb’s hips, pinching lightly at Caleb’s ribs on one side to get him to move, gasping as the clamps and weights pinch and swing. Molly returns a moment later, handing him the cage, and Essek thanks him before turning to the man before him.

“I told you this would stay on until I saw fit to remove it,” Essek says, fitting it up and over Caleb’s cock, closing the metal band at the top and using a small lock to click it shut. It’s a fight for Caleb to keep his hips still, every light touch of Essek’s fingers, however impersonal, sending zings of frustrating pleasure to curl in his belly. Once locked, Essek lets go, and the weight of the cage tugs down. Caleb groans, arms flexing behind him.”How long that is greatly depends on how well you please us. Though, no matter how well you do-” Essek reaches a finger out to trace over and between the bars of the cage, drawing a low cry from Caleb. “You aren’t coming tonight.”

He withdraws his hand, and Caleb tries to pull himself together, knowing Essek expects a response. “As you wish, sir.”

“Yes, it is.” Essek pushes him back with a soft hand on Caleb’s stomach and rises to his feet. He moves Caleb to the center of the room and just observes him a moment, walking around him in a slow circle.

Caleb prickles with the heat of Essek’s regard, as well as the arousal still simmering under his skin. Knowing he doesn’t get to come tonight is doing nothing to quell his desires, instead stoking them higher.

Molly waits, leaning on a bedpost, tail swishing in anticipatory curls low to the floor, moving closer as Essek beacons him.

“Lovely blossom-” Essek pulls Molly in and kisses him, hands going to frame his face. Molly leans into it, and all Caleb can do is watch, wishing he could touch.

They pull apart after a moment, and Molly’s breathless when he asks, “Yes, sir?”

Looking over his shoulder at Caleb, but still addressing Molly, Essek smiles. “How would you like to take your pleasure this evening?”

Ears and tail perking, Molly bounces over to Caleb, taking him in as well, though from a much closer distance than Essek did, reaching out to drag fingers and claws lightly over Caleb’s arms, sides, ass as he goes. He takes a second to set both of the clamp weights swinging gently, pulling a groan from Caleb as he hunches forward.

“Posture, pet.”

With a whimper Caleb stands up straight again, meeting Molly’s impish grin. Molly reaches up, cupping the side of Caleb’s face before rubbing his thumb over Caleb’s lower lip.  
“Hmm. Mouth I think, sir.”

“In that case-” Essek’s eyes look between them, calculating. “Give me a moment.”

He guides Caleb to his knees, bidding him to wait. Grabbing a bar from their cabinet, he hands it to Molly. “Hold it in two hands, up in the air, as far as you can reach with your feet flat on the floor.” Molly complies, and Essek floats up and a second later the bar is held suspended in the air, a streak of gold dust down the length of it. Essek settles back to the floor and places a hand on Molly’s side, stroking over warm skin and muscle before undoing the button over Molly’s tail and the lacing on Molly’s leggings. He tugs them down over Molly’s hips, freeing his cock. “You’re to keep your hands on the bar. If you let go, he stops.”

Molly licks his lips, getting a better grip on the bar as a shiver goes through to the tip of his tail. “Yes, sir.”

Looking down at Caleb, Essek makes sure he has eye contact. “If I tell you to stop, you stop and pull back. Understood?”

His own situation is pretty dire, his cock throbbing between his legs, nipples twinging, but Caleb can’t help but smile as he looks up the trim line of Molly’s body. “Yes, sir.”

“Then you may begin.”

Rising up on his knees, Caleb leans forward, wincing at the pull and swing of the clamps before taking a moment to catch Molly’s cock with his lips, since he can’t use his hands and Molly can’t help him. Once he does, though, he sucks, using that to help him draw it further into his mouth. He teases with swipes of his tongue, pulling back just so he can bob forward again, and in a few minutes he’s got Molly fully hard, a pleasant weight on his tongue. Molly’s hips keep twitching forward, though Caleb thinks he’s trying to control himself.

Well. He’ll see about that.

He pulls back until just the head is in his mouth and begins swirling his tongue around it as lightly as he can while still making contact, pausing every ten seconds like clockwork to flick underneath.

His efforts are rewarded as Molly’s movements get more frantic, and while he can’t easily see much, the rasp of Molly’s heavy breathing and moans coincide with the throbbing pulse and twitches of Molly’s cock on his tongue to give him a pretty solid idea of how close Molly is.

And he’s _close_.

Any moment now, he expects Molly to come, and he has a feeling Molly feels that way, too, when he hears Essek clearly say, “Stop.”

Caleb immediately pulls back, letting Molly fall from between his lips, and there’s a howl from Molly.

“ _Nng-_ but- sir, I didn’t let go!” Molly sounds fraught, and when Caleb tilts his head up to look, able to freely to do so, Molly is still gripping onto the suspended bar, chest heaving and body trembling, tail moving in tight frustrated coils.

“That is true.” Essek floats over and pats Molly lightly on the cheek before ruffling his fingers through the tiefling’s hair. “I felt like being a bit mean tonight as well. You were _very_ inspiring.”

Molly groans, head dropping down with a quiet sound, but doesn’t let go of the bar.

Turning to Caleb, Essek says, “You may continue as you were, spark.”

“Of course, sir,” Caleb says, smiling and he meets Molly’s gaze long enough to catch his scowl. Snorting a laugh, Caleb gets back to work.

It doesn’t take long to get Molly worked up again, the moans and cries tumbling from his mouth faster and faster the closer he gets. At one point he shouts, hips jerking forward suddenly, and a surprised sound makes it out of Caleb despite his mouth being full.

“My apologies, pet.” Essek’s voice floats around from just behind Molly. “I just thought our blossom might like a taste of what you had earlier.”

Unable to answer, Caleb just hums in response, which earns him another twitch of Molly’s hips and a choked gasp.

It soon becomes a give and take, Molly beside himself with Caleb on one side, and Essek on the other. Caleb isn’t sure what Essek is doing, but it must be quite something because Molly is almost sobbing in need, twisting and desperately holding onto the bar above.

“ _Oh gods_ \- please- sir- _aaah_ \- I can’t-”

“Pet,” Essek calls again, voice just loud enough to carry. “On the count of five, do your worst.”

Caleb starts to count in his head- _eins, zwei, drei, vier-_ Molly whimpering above him, and when he hits _fünf_ he does as instructed, leaning up and forward, ignoring the increased pull on his nipples as he relaxes his throat and swallows Molly down, doing his best to vocalize around him.

That and whatever Essek does is enough to send Molly screaming into his orgasm, hips bucking helplessly.

Caleb moves with him, swallowing him down, and continues, though slowing as Molly starts to come back down. Just as Molly is starting to whimper from oversensitivity, Essek instructs Caleb to stop, then helps the tiefling let go of the bar, guiding him over to sprawl in a heap on the bed, carding his fingers through Molly’s hair and whispering something quietly to him.

Meanwhile, Caleb sits back on his heels, moving his jaw around. He knows he’s not done; Essek still hasn’t had his own satisfaction yet, and he can’t imagine that this is the full extent of his price for failure.

As expected, Essek makes his way back over a minute later and gazes down at him, a predatory expression on his face. “Don’t you make a lovely picture like this. There are times I think I should just keep you this way, locked up, and needy. See how many days it would take for you to beg me to let you out of the cage.” He steps closer and Caleb’s mouth goes bone-dry, head tilting up to follow Essek’s approach. “How long I’d have to tease you until you didn’t remember your own name.”

His voice doesn’t get any louder, still quiet and even, but _gods_ , the _words_ this man says. Caleb feels his cock twitch as his excitement starts to ramp up again. He has to close his eyes, to look away, to breathe, but that doesn’t help; it only lets his imagination run wild.

Imagining being locked in the cage for days at a time instead of hours.

Imagining Essek torturing him with pleasure until he can’t do anything but beg, and then being told ‘no’.

Until the only name he remembers is Essek’s.

He shudders all over, the wave of arousal that hits him enough to drown in.

“For now, though-” Stepping up to stand just in front of him, Essek reaches down and catches Caleb’s chin gently in his fingers, tilting his face a little higher. “On your feet, pet.”

It’s more difficult with his arms bound, but not _too_ difficult for Caleb to stand; he tries to move slowly, smoothly, so as not to jostle the weights on the clamps too much. He’s led to the foot of the bed, and Essek relieves him of the weights, running a light fingertip over one red and tender nub. Caleb twitches, trying to hold position, to not pull back. Essek meets his eye and his touch grows firmer, increasing stimulation until Caleb’s biting his lip, fingers clenching into fists behind him.

“Lovely.” He reaches up, fingers on the two beads that cinch the clamps closed. “Deep breath, spark.”

Caleb takes a deep breath as told, and as he starts to let it out Essek tugs, releasing the hold the clamps have on him. His breath rushes out of him as a groan as blood rushes back in, arms flexing as he tries to process. He doesn’t realize he’s hunched forward again until a light touch on his forehead gently pushes him back upright. As he unfolds, the rope strands to either side of his nipples rub and tighten, pulling a breathy sound out of him.

“Now then, pet, face the bed.”

He moves to comply, and widens his stance to shoulder-width as Essek taps the inside of his thighs. A gentle hand between his shoulder blades presses him forward until he ends up with his upper body supported by the bed. He knows, objectively, that the coverlet on the bed is soft and comfortable, but to his abused nipples every sensation seems amplified, sending jolts of pleasure-pain straight to cock. He buries his face in the bedding, groaning, and a second later feels claw-tipped fingers brushing through his hair.

Turning his head to look up he finds Mollymauk has recovered enough to move, laying down so that he’s oriented towards Caleb. The look of glee from earlier has softened somewhat, and he looks downright fond.

He spends a few minutes petting Caleb’s hair and murmuring ever-more ridiculous endearments to him in a smattering of languages as Essek gets undressed and retrieves the bottle of oil they keep in the nightstand.

Caleb thinks he’s calmed, that he’s cooled off, but then there’s the touch of Essek’s hand smoothing over his ass and Caleb finds he can’t help but press back into it.

“So eager, my spark.” 

The hand on his ass pulls away, and for a moment there’s nothing- until there’s a gentle brush of oiled fingertips over his balls and Caleb yelps, going up on his toes in surprise. A hand finds the ropes between his wrists, tugging him back down, and it stays there until he’s settled once more.

Essek’s hands find his ass again, and one oiled fingertip starts to circle at Caleb’s hole. The touch is light, teasing, and Caleb whines, once more turning his face down into the blanket beneath him. He desperately wants to press back to coax Essek’s finger inside, but it’s pointless. Even if he knew Essek wouldn’t just pull his hand away, Essek won’t be rushed any faster than he intends to go anyway.

The finger circles longer, far longer than Caleb knows is necessary, pulling back a couple times more to be coated in slick, and his thighs are trembling from the effort of staying still by the time the finger slowly, _finally_ , presses in.

As in most things, Essek is patient to a fault, taking his time because he can, and because he knows it will torment Caleb all the more. Eventually he has two fingers in, and he crooks them, searching, and Caleb convulses when Essek finds his target. He’s merciless, teasing, slowly swiping a fingertip back and forth until Caleb’s squirming and pleading for mercy, hands clenching and unclenching behind him.

Patient as he is, even Essek has a limit. His fingers withdraw, leaving Caleb shuddering with want just long enough to thoroughly oil himself before starting to press in, hands gripping at Caleb’s hips to hold him steady. He doesn’t prevaricate, done with teasing, ready to take his own pleasure, and all Caleb can do is try to brace. He doesn’t bother trying to stop the noises he’s making, knows that’s a losing battle from the outset. Sensation threatens to overwhelm him, and he lets it- the slick slide of Essek as he thrusts in and out of him, the occasional lightning-like bolts of pleasure when Essek hits his prostate. The scratch against his nipples from the fabric as he’s driven forward with each thrust, the maddening arousal he can’t relieve-

All of it combines into a tidal wave, and instead of fighting the current he gives in and rides it forward.

He’s vaguely aware of Essek coming, grip tightening to bruising at his hips, but it’s distant, as is the fizz of the magic Essek uses to clean them both up. Every direct touch lights him up, zings of sensation that make him gasp and writhe. There are hands in his hair again, soothing, as the ropes at his wrists come loose and unwind. There’s the feel of magic lifting him slightly and soon the chest harness is gone as well. Essek floats him all the way up onto the bed, depositing him next to where Molly’s now laying, then climbs up onto the bed on Caleb’s other side.

They sandwich him in, and by some unspoken agreement both end up draped partway over him, legs tangled with his and arms twined together. Essek pets over Caleb’s stomach while Molly’s tail winds around an ankle.

Caleb floats, everything soft and fuzzed at the edges, all the touch feeling lovely, and when Essek’s hand brushes lower, dragging a finger over the bars of the cock cage, grazing him, all he does is gasp, arching slightly in their hold before settling back down into a quiet hum.

Slowly, he comes back to himself, body sore, feeling pleasantly well-used. The low hum of arousal is still there, just below the surface, sparking up everywhere they touch, but it’s manageable.

For now.

Essek’s fingers trace over the marks on his wrists from the ropes, trailing up to his chest and coming to rest over his heart, tracking his pulse, no doubt.

“Are you well, my spark?”

He doesn’t have the words just yet, so he nods instead, humming contentedly while clumsily trying to pat Essek’s hand. There’s a huff of amused laughter, and he’s pleased when the petting starts again.

“You’ve taken your loss very well. You may yet have the cage off tomorrow.”

That’s sooner than he’d expected, honestly, but as he sinks further into the bed with Molly’s fingers trailing up the inside of his thigh making him gasp, he knows tomorrow is still a long way away.


End file.
